8 Tips to Better Manage Freelancers

David Freund

David is the Director of Web Development with Junto, a digital agency powered by freelancers. When he's not running the day-to-day operations at Junto, you can find him exploring the Rocky Mountains by bike or snowboard.

The opportunities for contract hires are booming and shouldn’t be ignored. From one-off creative gigs to fractional finance managers, there have never been more opportunities for companies to capitalize on the booming gig-economy. At Junto, we’ve been collaborating with freelancers over the past few years and learned invaluable lessons along the way. Below you’ll find our best insights to ensure that your next freelance hire is a success.

1. Don’t fall for the misconceptions

The first step towards collaborating with the gig-economy is getting your mindset in the right place.

“If you’re looking for a thousand ways to be a skeptic about the idea of outsourcing, you’ll sure as hell find them.”

We seem to only hear the horror stories from outsourcing.

“We lost control over our project”

“The code quality was garbage”

“They didn’t understand the requirements”

While issues like this are bound to happen, they’re almost always due to inexperience. Companies should understand the exact requirements for the freelancer and manage every step of the way. We’ve seen it a dozen times, where an ill-equipped digital agency lands a web project and goes into panic mode looking for a freelancer to help. Hearing some of these horror stories, it’s easy to understand why a company would shy away from the idea of bringing in freelancers to help. However, the estimated 2.3 million U.S. jobs being outsourced reveal it’s only a matter of time before contract hiring becomes the new standard. Don’t fall for the misconceptions, plan and manage accordingly for a successful project.

2. Own your project and learn from your mistakes

It’s imperative to remember that a freelancer’s performance depends on your ability to manage the project. As you would hiring your first full-time employee, you’re bound to make mistakes and overlook critical steps along the way.

“If and when things go wrong, don’t be quick to point fingers at the developer. This is exactly where the misconceptions of working with freelancers come from.”

If the project didn’t come back to specification, then you should have better communicated the scope of work. If the developer wasn’t capable of fulfilling the task, you should have spent more time vetting. Fail fast, improve your processes, and you’ll be reaping the benefits of working with freelancers sooner than you know it.

3. Don’t overlook the importance of onboarding

We were guilty of this for the first 6 months of running Junto. We would spend 80% of our time vetting new freelance hires, but completely overlooked the importance of onboarding.

Take time to familiarize freelancers with every element of your business that you feel will contribute to a project’s success. To save time, create an onboarding video using screen recording software like Loom or Screen-Cast-O-Matic. It’s not perfect by any means, but our onboarding video welcomes the new team member and walks them through our processes from start to finish.

4. Visuals are a universal language

For some of our team members, English can be their second or even third language. To simplify communication, we look for those who are fluent in English in our vetting process. However, dialects and cultural values can still result in occasional miscommunication.

To avoid any confusion with project feedback we strive to support task feedback with visuals such as screenshots and mockups. This helps to provide more context for them to better understand. Subjective comments such as“move this a little bit up” or “make this slightly bigger,” can spiral out of control without visuals. If you don’t have Adobe CS skills, don’t sweat it. A screenshot tool likeSnappy and the preview app on Mac will allow you to get the job done.

For more complex tasks, we’ll resort to screen recording software such as Loom or Screencast-O-Matic. You can even password protect the videos to ensure privacy.

5. Design systems to mitigate risk

Bringing in freelance help has its clear advantages. However, it can also add another layer of risk to a project’s success. There’s enough angst around client-facing work as is. It’s imperative to design systems to mitigate risk where possible. For example, when working with a new freelancer, we always schedule early check-ins on the project to ensure everything is on track. If and when things go wrong, always have a reliable backup resource in mind.

If you don’t have the required knowledge or experience, consider bringing in an expert to oversee the project management. Tasks such as pushing a site live, implementing technical SEO elements, or setting up conversion tracking can come with critical consequences if not done correctly.

It’s imperative to think and act on the idea that a freelancer is a long-term investment in your company’s success. This all begins with setting expectations and trusting one another to get the job done. You should treat the freelancer as an extension of your team. Use words like “we” and “us” instead of “I” and “you” to build a team mentality. Encourage open-mindedness and always acknowledge a job well done, just as you would for an internal team member.

7. Establish the proper tools and time blocks for real-time messaging

In today’s workforce, tools like Slack and Google Hangouts are commonplace. In the beginning of a relationship with any new freelancer, we establish a real-time messaging tool to discuss project details. AtJunto, we work with freelancers all over the world, so we’ve learned early on to establish designated chat times in overlapping time zones. Our team has dedicated time blocks throughout the day where they discuss outstanding items and project details as needed.

8. Don’t expect a unicorn

Similar to building a house, a successful project will require multiple specialists. You wouldn’t expect an electrician to handle your interior design. Don’t hire a freelance web developer with the expectations that the site will be designed, developed, and delivered SEO optimized.

I’m not saying that these unicorns aren’t out there. Just don’t set expectations around these ideals. Instead, identify which steps of the project should be outsourced and which can be completed in-house.

Following these guidelines have helped us to successfully scale our freelance team to over 25 part-time team members from all over the world. When hiring and working with freelancers, don’t be discouraged if you don’t get it right the first time. The most important lesson is to learn from the mistakes and quickly improve your processes for the next time around. The gig economy isn’t going anywhere, so the sooner your business learns to collaborate with it the quicker you’ll begin reaping the benefits.

Interested in learning more? Check out another post we wrote about the booming freelance economy.

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